Holiday rentals with a pool in Manatee County

Mossy Oak Ranch - Near Terra Nova Equestrian Ctr

Mossy Oak Ranch a one of a kind 5-acre resort-style tropical getaway with a farmhouse country decor. Enjoy the quiet and peacefulness of the country life. A short distance to Siesta and Lido beaches. Located minutes away from Myakka State Park and Terra Nova Equestrian Center. Includes a magnificent resort-style salt water pool, waterfall and cave to escape the Florida heat. Take in the pristine Caribbean colors of the water while enjoying a cocktail at the Tiki bar, an unforgettable vacation.

Sport & Wellness Getaways

Perfect for large families or group getaways, this luxury retreat features a private pool, game room, and expansive outdoor spaces. Highlights: * On-site property manager * Private pool and outdoor shower * BBQ area and large patio * Game room for all ages * Fully stocked kitchen * Unlimited outdoor parking + 2 covered spaces * Access to: 6 tennis courts (5 hard, 1 clay), 4 pickleball courts, 1 sand volleyball court * Shared Courtyard restrooms

Sun-Kissed Memories: Open Thursday, March 26th!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Garden Home/Heated Pool/King-Bed/20 min Beach/Pets

Nestled beneath towering trees, this cozy 3-bedroom, 2-bathroom home offers a peaceful getaway. The screened-in heated pool and patio provide a quiet spot to relax and enjoy nature’s beauty in privacy. With new beds and many thoughtful amenities, it’s a comfortable retreat for your stay. Whether you're swimming, grilling, or simply enjoying the surroundings, this home offers a calm atmosphere to unwind and share time with family or friends in complete comfort. Message us with questions.

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

Pickleball - Heated Pool - Relax, Play & Grill

- FREE POOL HEAT, private pool - PICKLEBALL COURT in our back yard. - 2 King Beds, Queen sleeper sofa, 2 bunk beds - Close to Anna Maria Island - 7.3 miles to IMG Academy - Large back yard fully fenced - BBQ Grill - Outdoor TV - Corn toss - Ping Pong - Boardgames - Outdoor dining table - 1 mile from Robinson Preserve: kayak rentals, nature hiking, running, and playgrounds - Beach chairs, beach towels, cooler, umbrella provided. - pack n play, high chair - Smart TV in every room

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

Orange Oasis: Clean, heated pool, near beaches.

Enjoy your little slice of paradise at the beautifully decorated Orange Oasis! 3 bedrooms & 2 baths, plus a daybed with trundle. Heated Pool. High speed wifi & 4 TV's all with Hulu, Apple TV, Disney+, & ESPN. Vaulted ceiling, rainfall walk-in shower, washer & dryer, large fenced backyard, pool, garage parking, Weber grill, & a quiet safe neighborhood. The home comes fully stocked with Ziploc bags, cooking/kitchen essentials, coffee, beach essentials, & outdoor/indoor games.

Beach, Village, Dock & Private Pool! One-of-a-kind

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

Saltwater heated pool w/ massage chair + hot tub

Welcome to Citrus & Serena Stays, your private tropical oasis perfect for large families or groups! Near Bradenton’s attractions, including Anna Maria Island, this property features a screened-in heated saltwater pool, electric massage chair, fire pit, and more. With its playful orange-fruity décor, it’s ideal for an unforgettable vacation ☀Bradenton Beach - 12 Min ☀Riverwalk - 10 Min ☀Anna Maria Island - 12 Min ☀IMG Academy - 10 Min

Spacious Gated Townhome w/Pool Access Near Beaches

Welcome to your Florida getaway! This spacious and beautifully maintained townhome is located in a quiet, gated community just a short drive to the area’s stunning Gulf beaches, restaurants, shopping, and attractions. Whether you're visiting for beach days, family time, or a peaceful retreat, this home offers comfort, convenience, and everything you need to settle in.